Beautiful Risk
by Querel
Summary: Dave decides to try something different when his boyfriend comes over to visit. Something that's special and soft and…pink. Bottom!Dave. Crossdressing.


Dave stood in the bathroom, staring at himself with his teeth digging into his bottom lip. They'd been there for the past twenty minutes and were making a rather impressive dent, red and stinging just a bit.

He took his shades up from the bathroom counter and slid them onto his face. His lungs expanded, aching with air in his chest before it was all expelled in a giant sigh. In the other room, his cellphone chirped a text message alert at him.

That would be John.

Dave's heart startled inside his ribs, sending a flurry of bubbles and butterflies through his stomach. Which, upon consideration, sounded really girly. Dave figured at this point, it was only appropriate. He picked up the cellphone and read,

'_i'm here!'_

Dave texted back '_come on up the door is unlocked_' after struggling with the buttons and nervous fingers. He didn't want to go to the door. Not like that. Instead, he crawled up onto his bed and looked towards the window.

It was evening. The late winter sun bled through the glass and into the dark and cluttered bedroom. Dave knelt, his spine straight as he stared outside, trying not to shake.

He wanted to convince himself: there was no reason to be nervous. But really, Dave could only believe that he was wrong. It was a risk. A big one. He had no idea if it would work but he had already made his decision.

Striders never back down.

"Dave!"

The excited call through the apartment made Dave jolt a bit, but he didn't move. Just kept still with his face to the window, waiting with a heartbeat like a thrashing beast in his chest. Heavy. Hot.

"Dave, I brought you some apple juice because I loooooooove yoooooooou. I'm putting it in your fridge, okay?"

Dave swallowed.

"Yeah, sounds good, Egbert."

"Oh, jegus fuck, you and your shitty swords!" There was continued clattering from the kitchen as John tried to find a space to stow his gift. Dave couldn't help but smile.

"Thought you woulda learned by now," he called, glad that his voice didn't crack.

"Yeah, well, sometimes I like to think you're normal somewhere deep inside…."

John's voice came nearer. Dave's heart clenched; he took a deep breath.

"What are you doing sitting here in the dark?"

It was obvious that he didn't need to answer that question. John's voice trailed off as he stumbled over the junk in the doorway and caught sight of Dave on the bed.

"O-oh…."

When Dave turned his head, he was smiling, slick as ever, eyebrow flicked up in intrigue.

"Hey, sweetcheeks," he said quietly. "Come here."

"Dave, you're wearing a dress."

John gaped at Dave with wide, unblinking eyes, slowly drawing nearer to the bed. White thigh-high stockings disappearing under short skirts in pink with fluffed petticoats. A silk sash in bright red around a narrow waist tied in a bow at the small of his back. Blush pink damask patterns lined with white Chantilly and bunched up at the hips to reveal the underskirts. A white blouse, pleated at the breast with loose and billowy sleeves. And a red velvet ribbon tied around his neck in a drooping bow.

All set off with the characteristic aviator shades.

John blinked again, settling on the bed as he looked Dave up and down, his eyes finally resting on Dave's face.

"What…," he started in a whisper. But he couldn't find the question he wanted to ask. "…why? Is this…some sort of demonstration of your rad irony?"

Dave smiled. One of those rare, real ones that didn't hide anything.

"Good boyfriends don't need irony to make the magic happen."

"Yeah, but why are you wearing a dress, _boy_friend?" John asked, grinning as he pulled Dave down next to him, touching their foreheads together.

"Long-time fantasy of mine," Dave muttered.

"Really?" John asked. "Well, that explains your sudden interest in white gloves and tiny hats." They laughed, quiet chuckles tumbling back and forth between the two of them. John lifted his hands to hold Dave's smiling face and kiss him. "Might be weird for saying this, but it actually looks really good on you."

"Knew it would," Dave murmured, nuzzling at John's hair.

"You liar; you were scared shitless. Shoulda seen your face, I thought you were gonna burst into one of your random, defensive rounds of slam poetry."

"It's called improving."

"It's dumb."

Dave pulled back, settling into the loose hold of John's arms around his hips, pouting. John giggled at him.

"Please tell me that you're not going to bone me in a dress," he chuckled into Dave's ear. "I don't actually think it would be very romantic for my first time."

"Actually," Dave whispered back, his voice so quiet, the whir of the fan in the corner almost swallowed it, "I was hoping you'd bone _me_ in a dress for _my_ first time."

John's breath vanished from his lungs and slowly he retreated to look into Dave's eyes. He didn't have long to look, though. Dave leaned back in and kissed him. Over and over, lips, chin, cheeks and brow.

"Dave, come on; it's okay," John said gently, grasping silk-covered shoulders and stilling Dave so he could pull his shades off. "I shoulda known. You're not scared of anything." John looked into those red eyes, the shrunken, piercing pupils. "But you get scared when you show your softer side."

"Bullshit," Dave said, no volume to his voice at all.

"Yeah, well, stop it," John said, setting the glasses aside so he could press Dave to himself in a tight hug. "Striders have no reason to be afraid of dorks like me, right?"

"No one's afraid of dorks like you." Dave wrapped his arms around John's middle and kissed him again. Their lips met and moved together, Dave slipping his tongue past John's teeth to stroke gently along the roof of his mouth.

It would've been the best time to crawl into John's lap, straddling him and grinding down on what he hoped was a generously hard bulge in his shorts. But Dave had another idea. He pulled away instead, taking himself from John and backing away towards the wall.

John stared after Dave, looking puzzled and a bit worried.

"Chill out, Egbert," Dave said. A smile spread over his lips that tried to be condescending but got stuck around 'bashful' somewhere. "Just sit back and enjoy the ride for a minute."

Dave's middle finger pushed up the bridge of his nose like he did out of habit when he got nervous. But there were no shades to adjust, so he tried to pass it off as a scratch in the last second. John moved until he was leaning against the pillows, legs folded and smiling all dopey and precious like Dave just wanted to eat it off of him.

Fuckin' adorable.

Dave lifted the skirts in the front slowly, like he was unsure if it was actually a good idea. His eyes stared down at the card suit bed sheets where his knees dug into the mattress. John kept still, a captive audience member with his eyes fixed on the sight of the gradual reveal of Dave's thighs. Where the stockings ended, there were pink-ribboned garters. Internally, there was a part of John that was impressed by how much Dave invested into his costume.

The blond boy's skin was completely smooth: hairless. And it stood out even more when he had finally pulled the skirts all the way up, clutching the fabric against his chest. His cock strained, half hard in the hold of the baby pink panties he was wearing.

The garment was just a pair of plain, cotton, bikini cut underwear. But John could only think about how they held against Dave so snugly; the red light of the sunset outlined the hammocking fabric that cradled his balls and the sweet line of his erection, all the way to the gap where the fabric had been pushed away from his skin by how hard he was.

John's face shocked into a bright red. He could feel the heat radiating from the tip of his nose all the way across his cheeks and over his ears.

"Wow," he whispered, reverent. Until that point, John hadn't actually known that the sexiest thing on the planet was his boyfriend's erection in girls' underwear, so the realization pitched his brain into orbit. "Jegus…."

Dave took a shuddering breath, twitching in the confining cotton. The sheer fabric of the stockings stretched over his smooth, quivering thighs and he groaned gently, a slight sound of hesitancy.

John was catatonically enraptured, unable to focus on anything but the sight before him. So Dave took another stilling breath and got over himself.

He put the layers of fabric he'd been holding between his teeth to keep them up while his fingers slipped down the ruffled skirts, coming to rest at the freckled junctures between hip and thigh. Dave still couldn't bring himself to look at John's face—what he was doing was far too embarrassing and he didn't even have his shades on!—but he heard the low gasp when his fingers brushed over the protruding bulge of cloth and his aching cock beneath it. Dave stroked along the growing length with his fingertips, eyes squinting a bit as the elastic stretched and cut the beginnings of red chafe marks along his hips.

One hand teased slowly up and down the shaft, pausing at the head every now and then to feel along its ridge; the other fingered along the captive curve of his balls, sweeping back and forth along it. Dave stifled a moan at the back of his throat. A bead of precum bloomed through the cloth and dribbled down, leaving a darkened line of pink in its wake. At that point, Dave reached past the elastic and readjusted himself so the damp, crimson head of his cock peeked out over the lacey waistband.

John caught only a flashing glimpse of the sight before one of the underskirts slipped from the desperate grip of Dave's teeth and veiled it. Unwilling to be deprived of the beautiful display, John lunged forward, getting on all fours to crouch in front of Dave. He lifted up the white skirt and as soon as he found his treasure, John leaned in and wrapped his lips around the exposed flesh of Dave's erection.

Dave took his hands back, caressing John's face lovingly as his fingers withdrew to keep his clothes up. His mouth finally opened again and let out a long exhale, his head rolling back. John's tongue smoothed over the slit, licking up more precum before he dipped lower. With hot, damp breath, he mouthed at Dave's length, spending a particular time at the stain of cum, sucking gently at it and Dave's dick beneath.

"Nngh…."

At the caged moan, John looked upwards, hoping to catch Dave's gaze. Those red eyes were heavy-lidded, pupils blown so wide there was only a thin ring of scarlet around either one. Dave's normally pale cheeks were so flushed that John could barely see any of the freckles on his face.

So fucking beautiful.

The dark-haired boy reached under himself and pulled at his zipper, freeing his own erection without pausing at his attentions to Dave's succulent cock.

Dave's hips trembled and jolted. Every gentle press of John's lips against him, every stroke of that tongue made his spine quiver. His thighs tensed in warning.

"John…John," Dave panted, relinquishing a hand to muss it through John's hair. John paused. "Come up here," Dave whispered.

John smiled. Possibly at the double entendre, but whatever the reason, Dave's heart skipped a beat at the sight of it drawing near. He pulled John right to his chest, keeping his hoisted skirts trapped between them as he wrapped his arms tight around John's shoulders and kissed him.

John hesitated at first, unsure of how enthusiastic Dave would be about kissing a mouth that had been on his own junk but Dave's lips parted eagerly, practically pulling John's tongue inside, a moan at his every exhale.

John let his arms fall around Dave's hips, clutching at his ass. He tugged down Dave's panties until the fabric strained, tight around Dave's spread thighs but left his cock fully freed. Piano fingers slipped across the smooth, supple flesh of Dave's rear, dipping into the hot cleft of it before his palms came to rest at the sweet curves and gripped firmly. Dave keened and their cocks bumped.

"You have…no idea," John said, slowly pushing his hips back and forth, "how hot you are, Dave."

The hot boy in question buried his face into John's neck, sucking at his pulse heedlessly. He wanted to mark, leave big ugly bruises on that pale skin. Splotched that would be easily noticed and make other people ask questions. Questions that couldn't be answered without a blushing face, avoidant eyes and quickened heartbeats.

John's breath was warm and soft against Dave's neck. He kept a steady pace of his hips, gripping a little tighter at Dave's ass with each thrust forward. Their erections slid and slipped against each other with the gentle rustling of Dave's petticoats as a canopy.

Dave quickly found himself barreling towards the edge of his control as John's fingers drew closer and lower, reaching for those darker, hotter places of him. He pulled back from the hickey he left on John's neck and nosed for that sensitive spot: the one right behind the angle of John's jaw. Dave kissed it and licked it, canting his hips eagerly into the press of John's dick against him.

"So good," he breathed. John shivered.

"Dave, I wanna…." His movements gradually faded to complete stillness, leaving Dave to hold back the whine threatening to tumble off his tongue. They breathed against one another, heavy pants ghosting across skin and sweat-dampened clothes.

"What?" Dave asked, loosening his grip so he could look into John's eyes. As the wrinkled skirts fell down once again and the breath between them grew hot as it passed from their lungs, Dave felt a crawling urge slink up his spine and grip at him. "John, don't put me off for long; I'm losing my everything…."

"I just," John muttered, turning his head to one side so the fog in his glasses would clear. "You said—earlier—that I could…you know…." He grinned, tilted and hopeful, with a bit of unease looming in the depths of his eyes. Dave knew what he meant though.

He took another breath and then smiled back.

"Yeah, alright." Dave brought his hands to his blouse and started unbuttoning. John pulled his shirt off.

"You aren't gonna take it off, are you?" he asked as tossed the shirt aside.

"Like me in drag that much?" Dave asked, pausing after he got about six buttons down: enough to let the silk drape off his shoulders and reveal the pink of his nipples without the shirt falling away completely. Lightning flickered in John's hungry gaze.

"Might be my only weakness," he said, low and longingly. Dave's eyes lowered again and he bit his bottom lip to keep back the intensity of his smile. He shifted and fumbled a bit, John's hands resting on his shoulders as he watched and waited. Dave pulled the panties off one leg but let them dangle around an ankle as he stabilized again.

Before anything, he pushed on John's shoulders until he was laying back on the pillows and looked down at him. Beautifully ruffled boy, flushed chest and half-stripped with his cock dripping onto his stomach and his eyes wide in wonderment.

Dave leaned into him, wrapping his lips around John's nipple and sucking lightly at it. His tongue teased at the nub in feather-light flicks and soft circles. John gripped, one hand in the bunched sheets and the other threaded in Dave's hair, his head pressing back into the pillows as he moaned. Dave repeated his attentions to the other nipple, his free hand nudging against John's erection every now and then.

"Can't you, ngh!—can't you ever get to the point?" John moaned, dizzy at the soft feeling of Dave's hair brushing, cool against his bare skin.

Dave gave John's nipple a suckling kiss and flicked his eyes up to smile at John.

"Don't try to convince me you don't like it," he said.

Dave moved, reaching over to the bedside table and pulling open the drawer. From it, he retrieved a bottle of lube and then laid down at John's side, hiking the skirts up again.

"This part's gonna take a while," he grumbled, flicking the cap open and dousing his fingers with a squirt of lube.

"Can I watch?" John asked, sitting up and moving so that their previous positions were switched.

"I should start charging," Dave said, adjusting so he was lying on his back with his legs open.

"Just…shut up." The brunt of John's annoyance faded under the onset of his awe, watching Dave's wet fingers come around and spread the gel over the tight pucker of his hole.

Dave massaged at the dip for a moment, his fingertip moving in slow circles. Dave dared glances at John's face every now and then. The expression he found was frozen, rapt as it had been before in soaking in the spectacle before him, like it was the most amazing thing he'd ever seen.

Dave's blush deepened and his heart swelled. He knew... It was just so simple to see that John adored him: every weird and embarrassing part of him.

Another breath. Dave pushed his finger in. It was an easy thing. Didn't hurt at all but felt a bit strange. He watched as John's teeth bit down onto his bottom lip and his breath hitched a bit. From where he was propped up on the pillows, Dave could see the throb of John's erection, still hard as ever, angrily red from neglect.

Dave pushed his finger in and out, thinking more about John than himself. In all honesty, feeling the slicked digit slide back and forth within the grip of his sphincter muscle was just weird. It always had been. Without much prolonging, Dave pushed a second finger inside himself and continued.

"Have you," John suddenly asked, though it was only a whisper, as if he were sitting there watching a shy kitten that might run away at any moment, "Have you done this before?"

"A little," Dave said. "Figured it would make things easier." He lifted his knees a little higher, further exposing himself so he could push in deeper. Back and forth he went, turning and stretching as much as he could. It wasn't an easy thing. By the end of it, Dave knew he'd be sore no matter how much time he spent preparing.

"Give me a little more?" he asked, taking his fingers out and tossing the bottle of lube to John. The dark-haired boy blundered around with catching it, but eventually got the cap open. He hesitated though, looking up at Dave with a question he didn't ask. Dave waited, an eyebrow raised, but found his hand being pushed away.

John dosed some of the lubricant on his own fingers, muttering under his breath when the heady scent of strawberry filled his nose. He crouched and reached his hand out, touching carefully at the pink ring of flesh. Dave shivered, gathering his fingers in the bunched up layers of pink and white fabric at his waist.

John slipped two fingers in, slowly, coating Dave's insides with the stuff before reaching up to support one of Dave's quivering calves.

"Its soft," he murmured, entranced by the sensation. "I didn't think it would be soft…."

Dave clutched at his knees and moaned, his eyes closing. His cock ached and when John's fingers crooked up inside him, a suddenness burst through him. Like impulses of heavy heat that shocked from those deep and burning parts of him, all the way to his head where they erased thoughts and logic and everything else except John. John and how beautiful he was.

Dave gasped, trying to remember how to breathe.

"Good?" John asked, cautiously. "I didn't hurt you, did I?"

"No, no," Dave panted. "That was magic."

John beamed. He went right back to his job, moving his fingers in and out of Dave as the blond boy breathed slowly. He tried to relax when John said he'd be putting another finger in. John's digits were thinner than his own. Gentler. Tender in their care of him despite how stretched and invaded Dave felt.

"Don't think I can keep this up much longer," John chuckled softly.

"Y-yeah, that's fine," Dave said, coming down from another flash of pleasure that jolted through him when John brushed against that spot again. Without ceasing his push and pull, John bent and kissed at Dave's thigh. Again and again, right where the garter held to his freckled skin, all the way down until he reached Dave's hipbone.

Against the heat of his own face, Dave's cock was like a wet and burning brand. John smoothed his lips along the expanse of Dave's pubic bone, feeling the invisible prickle of the hairs that had started to grow back against the sensitive nerve endings at his mouth. He kissed and licked there, spending a particular amount of time tracing his tongue along the sweet curve where thigh blended into hip.

The candy flavor of strawberry stuck at the corner of John's mouth—a leftover smear—and he shared it with Dave in another long, wet kiss, taking that moment to stroke his three fingers against that sweet spot over and over. Dave moaned into John's mouth, barely sound enough to even kiss him back properly. John sucked on his tongue and then pulled himself completely away when Dave began to beg him to stop out of fear of coming too early.

Dave relaxed again, his legs falling from where he'd been holding them up (one with John's help) out of sheer force of will. The closeness of the fabric on his flesh made the heat linger even more and he watched in quiet concentration as John spread more of the lube on his own cock. Seemed to Dave like his break didn't last long and he went to hoist up his legs again.

"Wait just a sec," John said, putting his hands to Dave's to stop him. "Do this." He took Dave's stockinged legs and wrapped them around his own waist, smiling at him. Dave chuckled, reaching up to hold John's face as his ankles locked at the small of John's back.

"You know," he murmured, feeling the slight press of the head of John's cock against him as John shifted to steady himself, "I really love you." John blinked. "Completely and unironically."

Dave breathed a half sigh, smiling and worrying as he looked into John's face. He found only joy there, though. A pretty pink glow and a toothy smile that never failed to make his heart jump.

"I never thought I could love anyone or anything as much as I love you, Dave," John said. "So don't ever forget it."

He grabbed Dave's hands and kissed them both. Dave laced their fingers together and brought them down to the bed, a place for John to support himself.

John pushed in slowly and Dave's mouth fell open, his chin lifting as he gasped noiselessly. John's cheeks burned a darker red than they ever had. His fingers answered Dave's tight grip. Inch by inch, he pushed in until his hips met with Dave's rear and John's length was completely swallowed. He let out a breath he didn't know he was holding.

"You…" John whispered. It took him a few inhales and a couple trembling kisses along Dave's jawline to find what he wanted to say. "You're so perfect."

"John…." Dave shifted unconsciously, the sheer sensation of fullness unfamiliar to him and as his hips moved, he only made the sensation more obvious to himself. John, however, moaned softly into Dave's neck.

"You okay?" John asked quietly.

"Yeah. F-fine. You can move." Dave slid his hands from John's grip and wrapped them around his neck instead, wanting to hold as tight as he could, to be as near as he could, to touch every part that he could.

"I'll go slow," John assured him. And, like he said, John pulled carefully from where he'd been fully seated inside. All the way until only the head of his cock remained within the tight ring of muscle. Then he pushed in again, just as gently. Dave dug his fingers into John's shoulders, biting down on his lip to keep back the noise.

The sensation of John moving in and out of him was strange. A bit uncomfortable since nothing had never been so deep and hot inside of him. Dave could definitely see himself getting used to the feeling. Enjoying it, even. But for his first time, it was just an unfortunate oddity.

"Feel good?" he asked over the quiet groans that tumbled out of John's mouth.

"Amazing."

That was good. If John was feeling it, then Dave could definitely put up with however long it took to turn the oddity into a kink. One arm fell away from John's neck and went to Dave's dick, wrapping around it and pumping in an attempt to make himself completely hard again. It worked well. Dave focused a bit more on his own fingers and less on the slight burn as John rocked back and forth. He looked for a balance between the two, not wanting to pretend like John wasn't there, loving him.

It came easily when John stopped pushing as deep and instead, drew back to that spot. That wonderful place inside of Dave that kicked his head right off his shoulders and John thrust shallowly against it, the head of his cock rubbing in the most perfect way.

Dave opened his mouth and groaned desperately, his back bending in a gorgeous arc, unable to hold tight to John's shoulders any longer. His strength was sapped; at the beck and call of John's dick whenever it stroked along his prostate.

John himself was lost. Head full of sweet and wonderful things, just consumed by the heat and wetness of Dave's muscles around him. The forefront of his minds was just a haze of pleasure and every nerve fired. Feeling the tightening of Dave's legs around his middle, the echoes of his moaning as John pushed against his sweet spot and the full-blown glow of Dave's eyes, smoldering up at him.

John's breath hitched. His muscles strained.

"Dave…oh, it's so good…I'm gonna…."

"Come inside me, John," Dave moaned.

John swept his arms under Dave and pulled him up tight against himself as he came, a whimpered moan licking along the sweat-dappled skin of Dave's neck. Dave took lifted his own hands and hugged John back, his still burgeoning erection, smearing precum against the flat of John's stomach.

John kept still—paralyzed by the waves of pleasure that rolled through him—for a few moments before finally laying Dave back down to rest against the pillows once again. He slid out of Dave and watched blearily as Dave's mouth twitched at the odd sensation. Then he noticed how hard his boyfriend still was.

"Oh," John said, his heart suddenly dropping out of his body, "it wasn't good for you."

Dave's own heart cracked as the words whispered around him in a guilty circle.

"No, no, shut up," he protested, short of breath, reaching to find John's hands. "It was so excellent. Just not done yet, yeah?" He smiled. John smiled back.

"Let me, okay?" John said, squeezing Dave's fingers.

"Let you wha-oh!"

John grabbed Dave's hips and tugged them towards himself before practically flipping Dave back on his head. He slung Dave's legs over his shoulders and kneeled, looking down into Dave's face.

Dave blinked up at him, a bit stunned by the sudden movement. But then he watched as John shifted his focus.

John looked a little closer, right to the cherry-raw pucker of Dave's hole, leaking his own cum out and down the darkened flesh of Dave's cleft towards his back. He didn't think twice; John put his lips to Dave's abused hole and sucked at it, his fingers wrapping around Dave's cock and pumping slowly.

Dave cried out, surprised and ridiculously aroused. John's tongue slipped right inside of him, lapping at the mess he'd left behind as if it were the leavings of ice cream at the bottom of his cone. His slick fingers increased their pace, squeezing gently as they pulled back and forth along Dave's cock.

He was over the edge in a matter of second, crying out as cum shot straight down and splashed his face. The sensation shocked him a bit but did nothing to deter him. Dave moaned loud through clenched teeth and shut eyes, his hips shaking so hard that he only pushed up into John's face even harder.

John gripped at Dave's knees and lowered him to rest again, licking the remnants from his lips before looking down at Dave's face. He got himself good, ribbons of white trailing down his cheek to his chin and at his neck. Dave opened his eyes again and breathed, glancing at John with wet lips and dilated pupils.

John leaned in again and kissed him, not caring that he was getting cum on his face. Their tongues swept together in slow strokes as gentle aftershocks shuddered through Dave and he held tight to John. Together, they had little sounds of happiness and love, chuckles that they gathered between themselves when they pulled away and found strings of saliva and semen still connecting them.

John licked the cum away from Dave's face, murmuring how it only made him look more irresistibly delicious and Dave ran his tongue along the stain at John's own cheek.

John kicked off his shorts and boxers and started pulling thoughtlessly at Dave's dress.

"I like it a lot," he said, actually tearing runs in the stockings he was so desperate, "but I want you naked now."

"Chill out, Egbert, we'll get there," Dave scolded him with a laugh as he tugged off one garter and watched as John repeated the action. Then John peeled the stockings off, letting them flutter to the floor. The sash was pulled out and the skirts loosened, all pulled away by John while Dave worked the rest of the blouse off.

John immediately pulled Dave to himself again and lay down, twining their legs together.

"Dave," he whispered, putting his lips to that damp, freckled forehead, "I love you." John sighed. "I just do. You're fantastic and beautiful and I love you."

Dave held tight, his arms snug around John's waist.

"Does this mean I get to do you next time?" he asked.

John laughed.

"It absolutely does."


End file.
